A cycling gem


Go Back in Time


Go Back in Time


Go Back in Time


Go Back in Time

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Southern Tuscany Bike Tours


Our bike tours in Southern Tuscany, Italy features the Le Crete Senesi, Val d’Orcia and several hill towns.  Le Crete Crete Senesi literally means “Sienese clays” and the area gets its name from the distinctive, ochre-colored clay that dominates the ploughed fields.  This area also has some of the most scenic riding in Tuscany.


The breathtaking Val d’Orcia is an area so iconic of Tuscany that in 2004 the Valley was added to the UNESCO list of World Heritage Sites. The hill towns that you visit here include Montalcino, San Quirico, Pienza, and Montepulciano. All are charming towns; perfectly preserved within medieval walls.


This tour can be combined with our Central Tuscany Bike Tours that take you to Chianti, San Gimignano and the hills around Siena.



Best Time of Year for an Italian Tuscany Bike Tour


The best months to visit Tuscany, Italy are May through October when the temperatures are pleasantly warm and the risk of rainfall lower. In summer, temperatures are never stifling and there is often a pleasant breeze. Spring and fall are great times to ride but the risk of rain rises as you get into October. We do not recommend cycling here in winter.


Bike Touring in Southern Tuscany


Our Central Tuscany bike tours focus on the Val d’Orcia and visit the towns of Montalcino, Pienza and Montepulciano.   To provide a flavor of this tour, below is a description of one of the days bicycle touring in this region: riding from Montalcino to Montepulciano.


Montalcino to Montepulciano

Today you ride between hilltop towns across countryside so stunning it’s listed as a world heritage site.There are a number of great sites on the way from peaceful San Quirico to the rurally idyllic Montichiello. The latter is a fantastic place for lunch: after strolling around the quiet streets of this walled village, enjoy a leisurely lunch at a restaurant with a terrace looking south across the bucolic Val d’Orcia.

From lunch in Montichiello, it is a very manageable 7 miles to Montepulciano – so there’s no rush to finish your food.

Montepulciano is your overnight destination. The town is stunningly attractive from both afar (a cluster of red-brick buildings perched on a hilltop) and from within where the main street runs almost a mile along a narrow ridge. The topology of the town provides outstanding views of the surrounding countryside down alleyways and from the back windows of its many cafés and restaurants.

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Download Sample Itineraries

Tuscany 10-Day

Northern Tuscany

Southern Tuscany